Federal court documents say a campaign adviser to Hillary Rodham Clinton was personally involved in an off-the-books operation to help the former first lady’s 2008 presidential campaign in four states and Puerto Rico.

Federal prosecutors say District of Columbia Mayor Vincent Gray was aware of an off-the-books “shadow campaign” to support his 2010 bid and personally requested the funds from an influential District businessman.

Lawyers for a District of Columbia businessman at the center of a wide-ranging campaign finance investigation have asked the Supreme Court to take a case involving some of the documents seized from his home and office.

A Maryland businessman admitted in federal court Thursday that he was reimbursed for $160,000 in campaign contributions by his boss, who’s at the center of a wide-ranging investigation of political corruption in the District of Columbia.

A second person has been charged with making illegal campaign contributions at the behest of a District of Columbia businessman whose political activities are the subject of a long-running federal investigation.